[(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate

• ChemBase编号: 104775
• 分子式: C16H22O11
• 平均质量: 390.33928
• 单一同位素质量: 390.11621152
• SMILES: O=C(O[C@@H]1O[C@@H]([C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H](OC(=O)C)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13+,14+,15-,16-/m1/s1
• InChIKey: LPTITAGPBXDDGR-LYYZXLFJSA-N

名称和登记号

名称

• IUPAC标准名: [(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC传统名: [(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• 别名: 1,2,3,4,6-五-O-乙酰基-β-D-吡喃半乳糖; 五-O-乙酰基-β-D-吡喃半乳糖; β-D-半乳糖五乙酸酯; 1,2,3,4,6-Penta-O-acetyl-β-D-galactopyranose; Penta-O-acetyl-β-D-galactopyranose; β-D-Galactose pentaacetate; penta-O-acetyl-β-D-galactopyranose; β-D-GALACTOSE PENTAACETATE; 1,2,3,4,6-Pentaacetyl-beta-D-galactose; beta-D-Galactose pentaacetate

登记号

• CAS号: 4163-60-4
• EC号: 224-008-0
• MDL号: MFCD00063259
• Beilstein号: 98853
• PubChem SID: 24871841; 24848130; 162092306
• PubChem CID: 94752

理论计算性质

• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): -0.72691214
• LogD (pH = 7.4): -0.72691214
• Log P: -0.72691214
• 摩尔折射率: 81.6809 cm^3
• 极化性: 34.419 Å^3
• 极化表面积: 140.73 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: methanol: soluble50 mg/mL, clear
• 熔点: 139-144 °C; 142-146°C; 143-144 °C(lit.)
• 比旋光度: [α]20/D +23±1°, c = 1% in chloroform; [α]20/D +8.6°, c = 1.5% in chloroform; [α]24/D +23°, c = 1 in chloroform; +24 (c=4 in chloroform)

安全信息

• 保存条件: 0°C
• 德国WGK号: 1
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99.0% (TLC); 98%
• 级别: purum
• Empirical Formula (Hill Notation): C16H22O11

详细说明

MP Biomedicals - 02157180

Prepared from galactose
containing 0.5-5.0% glucose
Crystalline

Sigma Aldrich - 134031

包装
25, 100 g in glass bottle

Sigma Aldrich - 48270

Other Notes
选择性 1-O-脱乙酰反应1；选择性 β-1-C-烯丙基化反应2；立体选择性 β-硫苷化反应3

参考文献

• Regioselective 1-O-deacylation can be effected with ammonia in acetonitrile at ambient temperature: Synthesis, 1121 (1985).